17α-Hydroxypregnenolone: Difference between revisions
No edit summary |
Citation bot (talk | contribs) Add: s2cid. | Use this bot. Report bugs. | Suggested by Abductive | Category:Pregnanes | #UCB_Category 96/278 |
||
(51 intermediate revisions by 27 users not shown) | |||
Line 1: | Line 1: | ||
{{Short description|Chemical compound}} |
|||
⚫ | |||
{{Drugbox |
|||
| |
|||
| Verifiedfields = changed |
|||
⚫ | |||
⚫ | |||
⚫ | |||
⚫ | |||
⚫ | |||
| width = 250 |
|||
| image2 = 17-Hidroxipregnenolona3D.png |
| image2 = 17-Hidroxipregnenolona3D.png |
||
| width2 = 250 |
|||
<!--Clinical data--> |
|||
| tradename = |
|||
⚫ | |||
⚫ | |||
⚫ | |||
⚫ | |||
⚫ | |||
⚫ | |||
⚫ | |||
⚫ | |||
<!--Pharmacokinetic data--> |
|||
⚫ | |||
⚫ | |||
⚫ | |||
⚫ | |||
⚫ | |||
<!--Identifiers--> |
|||
⚫ | |||
⚫ | |||
| UNII_Ref = {{fdacite|correct|FDA}} |
|||
| UNII = 77ME40334S |
|||
⚫ | |||
⚫ | |||
⚫ | |||
⚫ | |||
⚫ | |||
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
||
| ChemSpiderID = 17215939 |
| ChemSpiderID = 17215939 |
||
| ChEBI_Ref = {{ebicite|changed|EBI}} |
|||
| InChI = 1/C21H34O3/c1-4-21(24)10-8-16-14-6-5-13-11-17(22)18(23)12-19(13,2)15(14)7-9-20(16,21)3/h13-17,22,24H,4-12H2,1-3H3/t13?,14-,15+,16+,17?,19+,20+,21-/m1/s1 |
|||
| ChEBI = 28750 |
|||
<!--Chemical data--> |
|||
⚫ | |||
| O=3 |
|||
| smiles = CC[C@@]2(O)CC[C@H]1[C@@H]3CCC4CC(O)C(=O)C[C@]4(C)[C@H]3CC[C@@]12C |
| smiles = CC[C@@]2(O)CC[C@H]1[C@@H]3CCC4CC(O)C(=O)C[C@]4(C)[C@H]3CC[C@@]12C |
||
| InChIKey = QPLFSAZMHUAMKE-FOCOMJRBBT |
|||
⚫ | |||
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
||
| StdInChI = 1S/C21H34O3/c1-4-21(24)10-8-16-14-6-5-13-11-17(22)18(23)12-19(13,2)15(14)7-9-20(16,21)3/h13-17,22,24H,4-12H2,1-3H3/t13?,14-,15+,16+,17?,19+,20+,21-/m1/s1 |
| StdInChI = 1S/C21H34O3/c1-4-21(24)10-8-16-14-6-5-13-11-17(22)18(23)12-19(13,2)15(14)7-9-20(16,21)3/h13-17,22,24H,4-12H2,1-3H3/t13?,14-,15+,16+,17?,19+,20+,21-/m1/s1 |
||
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
||
| StdInChIKey = QPLFSAZMHUAMKE-FOCOMJRBSA-N |
| StdInChIKey = QPLFSAZMHUAMKE-FOCOMJRBSA-N |
||
⚫ | |||
⚫ | |||
⚫ | |||
⚫ | |||
⚫ | |||
⚫ | |||
⚫ | |||
| molecular_weight = 332.48 g/mol |
|||
⚫ | |||
⚫ | |||
⚫ | |||
⚫ | |||
⚫ | |||
⚫ | |||
⚫ | |||
⚫ | |||
⚫ | |||
⚫ | |||
⚫ | |||
⚫ | |||
⚫ | |||
| melting_point = 268 |
| melting_point = 268 |
||
}} |
}} |
||
''' |
'''17α-Hydroxypregnenolone''' is a [[pregnane]] (C21) [[steroid]] that is obtained by [[hydroxylation]] of [[pregnenolone]] at the C17α position. This step is performed by the [[mitochondria]]l [[cytochrome P450 oxidase|cytochrome P450 enzyme]] 17α-hydroxylase ([[CYP17A1]]) that is present in the [[adrenal]] and [[gonad]]s. Peak levels are reached in humans at the end of [[puberty]] and then decline.<ref>{{cite journal | vauthors = Hill M, Lukác D, Lapcík O, Sulcová J, Hampl R, Pouzar V, Stárka L | title = Age relationships and sex differences in serum levels of pregnenolone and 17-hydroxypregnenolone in healthy subjects | journal = Clinical Chemistry and Laboratory Medicine | volume = 37 | issue = 4 | pages = 439–47 | date = April 1999 | pmid = 10369116 | doi = 10.1515/CCLM.1999.072 | s2cid = 41315909 }}</ref> High levels are also achieved during [[pregnancy]]. It is also a known [[Neuromodulation|neuromodulator]]. |
||
==Prohormone== |
==Prohormone== |
||
⚫ | |||
[[Image:DHEA1.svg|thumb|right|350px|17 OH–pregnenolone is converted from pregnenolone and gives rise to DHEA (below) and to 17 OH-progesterone (to its right)]] |
|||
⚫ | |||
This conversion is mediated by the enzyme 17,20 lyase. As such |
This conversion is mediated by the enzyme 17,20 lyase. As such 17α-hydroxypregenolone represents an intermediary in the Δ<sup>5</sup> pathway that leads from pregnenolone to DHEA. 17α-Hydroxypregneolone is also converted to [[17α-hydroxyprogesterone]], a prohormone for [[glucocorticosteroid]]s and [[androstenedione]] through the activity of [[3α-hydroxysteroid dehydrogenase]]. |
||
==Neurohormone== |
|||
There is some evidence that 17-OH-pregnenolone may have activity as a [[neurohormone]].<ref>{{cite journal | last1 = Matsunaga | first1 = M | last2 = Ukena | first2 = K | last3 = Baulieu | first3 = EE | last4 = Tsutsui | first4 = K | title = 7alpha-Hydroxypregnenolone acts as a neuronal activator to stimulate locomotor activity of breeding newts by means of the dopaminergic system | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 101 | issue = 49 | pages = 17282–7 | year = 2004 | pmid = 15569930 | pmc = 535386 | doi = 10.1073/pnas.0407176101 }}</ref> |
|||
==Clinical use== |
==Clinical use== |
||
Measurements of |
Measurements of 17α-hydroxypregnenolone are useful in the diagnosis of certain forms of [[congenital adrenal hyperplasia]].<ref>{{cite journal | vauthors = Riepe FG, Mahler P, Sippell WG, Partsch CJ | title = Longitudinal study of plasma pregnenolone and 17-hydroxypregnenolone in full-term and preterm neonates at birth and during the early neonatal period | journal = The Journal of Clinical Endocrinology and Metabolism | volume = 87 | issue = 9 | pages = 4301–6 | date = September 2002 | pmid = 12213889 | doi = 10.1210/jc.2002-020452 | doi-access = free }}</ref> |
||
⚫ | |||
[http://jcem.endojournals.org/cgi/content/full/87/9/4301]</ref> |
|||
⚫ | |||
== |
== Neurosteroid == |
||
17α-hydroxypregnenolone is a known neuromodulator as its acts in the [[central nervous system]]. Specifically, it is known to modulate [[Animal locomotion|locomotion]].<ref>{{cite journal | vauthors = Tsutsui K, Haraguchi S, Vaudry H | title = 7α-Hydroxypregnenolone regulating locomotor behavior identified in the brain and pineal gland across vertebrates | journal = General and Comparative Endocrinology | volume = 265 | pages = 97–105 | date = September 2018 | pmid = 28919448 | doi = 10.1016/j.ygcen.2017.09.014 | s2cid = 5636071 }}</ref> |
|||
⚫ | |||
== See also == |
|||
⚫ | |||
* [[Narave pig]], intersex pigs that have low levels of 17α-Hydroxypregnenolone |
|||
==Additional images== |
==Additional images== |
||
Line 61: | Line 72: | ||
</gallery> |
</gallery> |
||
==References== |
== References == |
||
{{ |
{{Reflist}} |
||
{{Steroid metabolism intermediates}} |
|||
{{Endogenous steroids}} |
|||
{{Xenobiotic-sensing receptor modulators}} |
|||
{{DEFAULTSORT:Hydroxypregnenolone, 17α-}} |
|||
[[Category:Pregnane X receptor agonists]] |
|||
[[es:17-Hidroxipregnenolona]] |
|||
[[Category:Pregnanes]] |
|||
[[ja:17-ヒドロキシプレグネノロン]] |
|||
[[ru:17-гидроксипрегненолон]] |
Latest revision as of 19:10, 8 March 2023
Pharmacokinetic data | |
---|---|
Metabolism | Adrenal, Gonads |
Identifiers | |
| |
CAS Number | |
PubChem CID | |
ChemSpider | |
UNII | |
ChEBI | |
CompTox Dashboard (EPA) | |
ECHA InfoCard | 100.006.239 |
Chemical and physical data | |
Formula | C21H32O3 |
Molar mass | 332.484 g·mol−1 |
3D model (JSmol) | |
Melting point | 268 °C (514 °F) |
| |
| |
(what is this?) (verify) |
17α-Hydroxypregnenolone is a pregnane (C21) steroid that is obtained by hydroxylation of pregnenolone at the C17α position. This step is performed by the mitochondrial cytochrome P450 enzyme 17α-hydroxylase (CYP17A1) that is present in the adrenal and gonads. Peak levels are reached in humans at the end of puberty and then decline.[1] High levels are also achieved during pregnancy. It is also a known neuromodulator.
Prohormone
[edit]17α-Hydroxypregnenolone is considered a prohormone in the formation of dehydroepiandrosterone (DHEA), itself a prohormone of the sex steroids.
This conversion is mediated by the enzyme 17,20 lyase. As such 17α-hydroxypregenolone represents an intermediary in the Δ5 pathway that leads from pregnenolone to DHEA. 17α-Hydroxypregneolone is also converted to 17α-hydroxyprogesterone, a prohormone for glucocorticosteroids and androstenedione through the activity of 3α-hydroxysteroid dehydrogenase.
Clinical use
[edit]Measurements of 17α-hydroxypregnenolone are useful in the diagnosis of certain forms of congenital adrenal hyperplasia.[2] In patients with congenital adrenal hyperplasia due to 3β-hydroxysteroid dehydrogenase deficiency 17α-hydroxypregnenolone is increased, while in patients with congenital adrenal hyperplasia due to 17α-hydroxylase deficiency levels are low to absent.
Neurosteroid
[edit]17α-hydroxypregnenolone is a known neuromodulator as its acts in the central nervous system. Specifically, it is known to modulate locomotion.[3]
See also
[edit]- Congenital adrenal hyperplasia
- Narave pig, intersex pigs that have low levels of 17α-Hydroxypregnenolone
Additional images
[edit]References
[edit]- ^ Hill M, Lukác D, Lapcík O, Sulcová J, Hampl R, Pouzar V, Stárka L (April 1999). "Age relationships and sex differences in serum levels of pregnenolone and 17-hydroxypregnenolone in healthy subjects". Clinical Chemistry and Laboratory Medicine. 37 (4): 439–47. doi:10.1515/CCLM.1999.072. PMID 10369116. S2CID 41315909.
- ^ Riepe FG, Mahler P, Sippell WG, Partsch CJ (September 2002). "Longitudinal study of plasma pregnenolone and 17-hydroxypregnenolone in full-term and preterm neonates at birth and during the early neonatal period". The Journal of Clinical Endocrinology and Metabolism. 87 (9): 4301–6. doi:10.1210/jc.2002-020452. PMID 12213889.
- ^ Tsutsui K, Haraguchi S, Vaudry H (September 2018). "7α-Hydroxypregnenolone regulating locomotor behavior identified in the brain and pineal gland across vertebrates". General and Comparative Endocrinology. 265: 97–105. doi:10.1016/j.ygcen.2017.09.014. PMID 28919448. S2CID 5636071.